Rittel, H. W. J., & Webber, M. M. (1973). Dilemmas in a general theory of planning. Policy Sciences, 4(2), 155–169.

This article lays out all of the uncertainty implicit in a certainty kind of problem. The author’s describe ‘Wicked Problems’. These problems do not lend themselves to linear problem solving techniques. There are ten ‘rules’ for a wicked problem, here I’ll include a section from rule 3. Solutions to wicked problems are not true-or-false, but good-or-bad.

There are conventionalized criteria for objectively deciding whether the offered solution to an equation or whether the proposed structural formula of a chemical compound is correct or false. They can be independently checked by other qualified persons who are familiar with the established criteria; and the answer will be normally unambiguous.
For wicked planning problems, there are no true or false answers. Normally,
many parties are equally equipped, interested, and/or entitled to judge the solutions, although none has the power to set formal decision rules to determine correctness. Their judgments are likely to differ widely to accord with their group or personal interests, their special value-sets, and their ideological predilections. Their assessments of proposed solutions are expressed as “good” or “bad” or, more likely, as “better or worse” or “satisfying” or “good enough.”
(p. 162)

This article is well worth reading in its entirety. It’s an eye opening exploration of what decisions look like in real life and is consciously setting itself against the ‘military’ view of problem solving.

Rittel, H. W. J., & Webber, M. M. (1973). Dilemmas in a general theory of planning. Policy Sciences, 4(2), 155–169. https://doi.org/10.1007/BF01405730